#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/06/2230616.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230616
loop_
_publ_author_name
'Liu, Lei'
'Song, Tao'
'Xu, Liang-zhong'
_publ_section_title
;
 (+-)-2-{3-[1-(2,4-Difluorophenyl)ethyl]-1,3-thiazolidin-2-ylidene}malononitrile
;
_journal_coeditor_code           DN2699
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1774
_journal_paper_doi               10.1107/S1600536811023737
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H11 F2 N3 S'
_chemical_formula_moiety         'C14 H11 F2 N3 S'
_chemical_formula_sum            'C14 H11 F2 N3 S'
_chemical_formula_weight         291.32
_chemical_name_systematic
;
(+-)-2-{3-[1-(2,4-Difluorophenyl)ethyl]-1,3-thiazolidin-2-ylidene}malononitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.508(2)
_cell_angle_beta                 90.940(2)
_cell_angle_gamma                112.861(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6886(14)
_cell_length_b                   8.9854(16)
_cell_length_c                   10.8188(19)
_cell_measurement_reflns_used    2422
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.11
_cell_measurement_theta_min      2.27
_cell_volume                     668.1(2)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4810
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.9313
_exptl_absorpt_correction_T_min  0.9220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0521P)²+0.2818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                2049
_reflns_number_total             2332
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2699.cif
_cod_data_source_block           I
_cod_database_code               2230616
_cod_database_fobs_code          2230616
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.28619(9) 0.70036(7) -0.03503(5) 0.0493(2) Uani d . 1 1 . .
F F1 -0.19221(18) 0.68270(16) 0.17886(11) 0.0523(3) Uani d . 1 1 . .
F F2 -0.3465(2) 0.44311(19) 0.52735(15) 0.0678(4) Uani d . 1 1 . .
C C1 0.2408(3) 0.8531(2) 0.07280(18) 0.0345(4) Uani d . 1 1 . .
C C2 0.0263(3) 0.7988(2) 0.36404(17) 0.0357(4) Uani d . 1 1 . .
N N1 0.2234(2) 0.8236(2) 0.18869(15) 0.0364(4) Uani d . 1 1 . .
C C3 0.1633(3) 0.9200(2) 0.29655(18) 0.0361(4) Uani d . 1 1 . .
H H3 0.0944 0.9755 0.2609 0.043 Uiso calc R 1 1 . .
C C4 -0.1470(3) 0.6816(2) 0.30078(18) 0.0380(4) Uani d . 1 1 . .
C C5 0.2315(3) 0.9856(2) 0.03016(18) 0.0366(4) Uani d . 1 1 . .
C C6 -0.2757(3) 0.5620(3) 0.3520(2) 0.0463(5) Uani d . 1 1 . .
H H6 -0.3904 0.4852 0.3063 0.056 Uiso calc R 1 1 . .
C C7 0.0653(3) 0.7939(3) 0.48932(19) 0.0419(5) Uani d . 1 1 . .
H H7 0.1785 0.8718 0.5365 0.050 Uiso calc R 1 1 . .
C C8 0.2460(3) 0.9825(3) -0.1015(2) 0.0439(5) Uani d . 1 1 . .
C C9 0.2356(3) 1.1362(3) 0.10832(19) 0.0409(5) Uani d . 1 1 . .
N N2 0.2449(3) 1.2619(2) 0.1680(2) 0.0598(6) Uani d . 1 1 . .
C C10 -0.2252(3) 0.5624(3) 0.4748(2) 0.0465(5) Uani d . 1 1 . .
C C11 -0.0604(3) 0.6760(3) 0.5452(2) 0.0476(5) Uani d . 1 1 . .
H H11 -0.0328 0.6746 0.6288 0.057 Uiso calc R 1 1 . .
C C12 0.3374(3) 1.0542(3) 0.3821(2) 0.0504(5) Uani d . 1 1 . .
H H12A 0.4102 1.0031 0.4156 0.076 Uiso calc R 1 1 . .
H H12B 0.2974 1.1161 0.4512 0.076 Uiso calc R 1 1 . .
H H12C 0.4140 1.1281 0.3335 0.076 Uiso calc R 1 1 . .
N N3 0.2605(3) 0.9831(3) -0.20641(19) 0.0652(6) Uani d . 1 1 . .
C C13 0.2830(4) 0.6928(3) 0.2078(2) 0.0634(7) Uani d . 1 1 . .
H H13A 0.4078 0.7428 0.2559 0.076 Uiso calc R 1 1 . .
H H13B 0.1944 0.6238 0.2558 0.076 Uiso calc R 1 1 . .
C C14 0.2883(5) 0.5919(4) 0.0852(3) 0.0751(8) Uani d . 1 1 . .
H H14A 0.1790 0.4861 0.0671 0.090 Uiso calc R 1 1 . .
H H14B 0.4023 0.5701 0.0861 0.090 Uiso calc R 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C14 . . 91.83(11) ?
N1 C1 C5 . . 129.40(18) ?
N1 C1 S1 . . 112.28(14) ?
C5 C1 S1 . . 118.31(14) ?
C4 C2 C7 . . 115.89(18) ?
C4 C2 C3 . . 120.40(17) ?
C7 C2 C3 . . 123.69(18) ?
C1 N1 C13 . . 114.67(16) ?
C1 N1 C3 . . 124.89(15) ?
C13 N1 C3 . . 120.28(16) ?
N1 C3 C2 . . 108.53(15) ?
N1 C3 C12 . . 110.00(17) ?
C2 C3 C12 . . 114.49(16) ?
N1 C3 H3 . . 107.9 ?
C2 C3 H3 . . 107.9 ?
C12 C3 H3 . . 107.9 ?
F1 C4 C6 . . 117.54(18) ?
F1 C4 C2 . . 118.02(17) ?
C6 C4 C2 . . 124.43(19) ?
C1 C5 C9 . . 125.92(17) ?
C1 C5 C8 . . 117.88(18) ?
C9 C5 C8 . . 115.58(17) ?
C4 C6 C10 . . 116.3(2) ?
C4 C6 H6 . . 121.8 ?
C10 C6 H6 . . 121.8 ?
C11 C7 C2 . . 121.7(2) ?
C11 C7 H7 . . 119.1 ?
C2 C7 H7 . . 119.1 ?
N3 C8 C5 . . 178.6(2) ?
N2 C9 C5 . . 176.8(2) ?
F2 C10 C11 . . 118.9(2) ?
F2 C10 C6 . . 118.0(2) ?
C11 C10 C6 . . 123.1(2) ?
C10 C11 C7 . . 118.5(2) ?
C10 C11 H11 . . 120.8 ?
C7 C11 H11 . . 120.8 ?
C3 C12 H12A . . 109.5 ?
C3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 N1 . . 109.3(2) ?
C14 C13 H13A . . 109.8 ?
N1 C13 H13A . . 109.8 ?
C14 C13 H13B . . 109.8 ?
N1 C13 H13B . . 109.8 ?
H13A C13 H13B . . 108.3 ?
C13 C14 S1 . . 109.04(17) ?
C13 C14 H14A . . 109.9 ?
S1 C14 H14A . . 109.9 ?
C13 C14 H14B . . 109.9 ?
S1 C14 H14B . . 109.9 ?
H14A C14 H14B . . 108.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.7490(19) ?
S1 C14 . 1.789(3) ?
F1 C4 . 1.362(2) ?
F2 C10 . 1.359(2) ?
C1 N1 . 1.335(2) ?
C1 C5 . 1.392(3) ?
C2 C4 . 1.386(3) ?
C2 C7 . 1.397(3) ?
C2 C3 . 1.519(3) ?
N1 C13 . 1.468(3) ?
N1 C3 . 1.488(2) ?
C3 C12 . 1.524(3) ?
C3 H3 . 0.9800 ?
C4 C6 . 1.375(3) ?
C5 C9 . 1.421(3) ?
C5 C8 . 1.425(3) ?
C6 C10 . 1.376(3) ?
C6 H6 . 0.9300 ?
C7 C11 . 1.387(3) ?
C7 H7 . 0.9300 ?
C8 N3 . 1.144(3) ?
C9 N2 . 1.148(3) ?
C10 C11 . 1.362(3) ?
C11 H11 . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.447(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12B Cg1 2_576 0.96 2.94 3.848(3) 158
